Enterprise Account Executive

Riderflex; San Francisco (CA); On-site; USD 300,000 - 350,000; Full time

Benefits offered by this job

Relocation support

Job summary

Riderflex is seeking an Enterprise Account Executive in the San Francisco Bay Area to build and grow new business revenue for a venture-backed voice AI company. This high-ownership role reports to the CEO and handles complex enterprise cycles end to end, turning pilots into production deployments.

You will lead discovery, design pilots with clear success metrics, and negotiate obligations with MEDDPICC, partnering with engineering, deployment, and product teams to ensure successful deployments.

Qualifications

• 5+ years of enterprise SaaS or AI sales.
• Track record closing $300K+ ACV complex deals.
• Experience selling to enterprises (CCaaS/CRM/AI).
• Proven ability to run long, multi-stakeholder cycles across IT, security, legal, procurement.
• Pilots with quantified business cases and ROI.
• Fluent in MEDDPICC and forecasting.
• Executive presence with engineering credibility.

Responsibilities

• Lead complex enterprise deals from first conversation to production agreement.
• Own discovery, solution positioning, business case, technical validation, procurement, negotiation and executive alignment.
• Translate customer operations and tech into a clear deployment roadmap.
• Design pilots with defined success metrics and drive them into production.
• Collaborate with solutions engineering, deployment, product and engineering to validate integrations and remove blockers.
• Stay accountable after signature, expanding use cases across teams and units.

Skills

Enterprise sales

MEDDPICC

Multi-stakeholder sales

Forecasting

Executive presence

Technical fluency

Job description

Location: San Francisco Bay Area, Peninsula. On-site, five days a week.
Type: Full time
Compensation: $300,000 to $350,000 on-target earnings (base plus commission), plus equity. Relocation support provided.

About the company

Our client is a venture-backed voice AI company building AI agents that handle the sales, support and logistics calls enterprise contact centers once staffed with large human teams. Thousands of companies run on the platform, including Fortune 500 names in healthcare, travel and technology. Revenue has grown more than tenfold since the start of 2025 with a team of about 50, and the company was recently ranked the top place to work in the Bay Area by a major business publication.

Their 2026 goal is a full CX platform where AI workers act as frontline agents, QA analysts and managers, improving every customer interaction rather than waiting for a human to retune them.

About the role

The company is hiring an Enterprise Account Executive to build and grow new business revenue. This is a high-ownership, hands-on sales role that reports directly to the CEO and works closely with the founding team. There is no playbook yet. This person creates pipeline, runs complex enterprise cycles end to end, and turns pilots into production deployments.

What this hire owns

Complex enterprise deals from first conversation to signed production agreement.

• Lead discovery, solution positioning, business case, technical validation, security and procurement, commercial negotiation and executive alignment
• Understand each customer's call center operations and technology stack, and translate them into a clear deployment roadmap
• Design tightly scoped pilots with defined success metrics and commercial next steps, and drive them decisively into production
• Qualify rigorously with MEDDPICC, multithread every strategic account, and keep forecasts accurate
• Quantify the business case: automation rate, resolution rate, cost reduction, customer experience and revenue impact
• Partner with solutions engineering, deployment, product and engineering to validate integrations and remove technical blockers
• Stay accountable after signature, working with deployment and customer success to expand across use cases, teams and business units
• Bring objections, competitive intelligence and product gaps back to product and leadership

What they are looking for

Must have:

• 5+ years of enterprise sales at a high-growth SaaS or AI company, with a track record of closing $300K+ ACV complex deals
• Experience selling technical products to enterprises, ideally contact center, CCaaS, CRM, communications infrastructure or AI
• Proven ability to run long, multi-stakeholder cycles across business leaders, IT, security, legal, procurement and executives
• Track record of designing pilots, building quantified business cases, and converting evaluations into large production deployments
• Fluent in MEDDPICC, multithreading, negotiation, pipeline management and forecasting
• Executive presence plus the technical fluency to earn credibility with engineering stakeholders

They thrive if:

• They have personally owned the entire cycle from outbound through signed agreement, consistently closing six- and seven-figure deals
• They can talk APIs, integrations and AI architecture with a CTO, then switch to ROI and automation rates with a COO
• They want an early-stage environment with no playbook and real ownership

Interview process

Four rounds: a recruiter intro call, a 30-minute phone round with the CEO, a 30-minute phone round with the COO, and a three-hour final onsite with the team.

Benefits

100% medical, dental and vision coverage, a daily meal credit, and monthly wellness, commuter, phone and internet reimbursements. The company sponsors work authorization for qualified candidates.